IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Comparison of fortified, sfursat and passito winemaking techniques for the enhancement of the oenological potential of the black grape cultivar Moscato nero d’Acqui (Vitis vinifera L.)

One of the key factors of the economical development of viticulture and wine industry in specific limited areas is the exploitation of ancient, local grape varieties. Therefore, in recent years the growing interest to rediscover minor varieties, previously cultivated, has promoted many studies. With this regard, the focus of this study was the Vitis vinifera L. cultivar Moscato nero d’Acqui, nowadays found only in old vineyards in the Acqui zone (North-West Italy). In particular, the aims of this work were: i) to investigate secondary metabolites profile of the grapes, and ii) to evaluate the attitude to the production of special wines.

Irrigation as a tool for heatwave mitigation: the effect of irrigation intensity and timing in Cabernet Sauvignon

Heatwave events, defined as 2 or more days reaching ≥ 38 °C, are an increasingly frequent phenomenon threatening grape production worldwide. Heat stress has been shown to have negative consequences on grapevine physiology, leading to increased evaporative demand and intensified water stress. Due to heatwaves overlapping with important stages of grapevine reproductive development, spanning from berry set to the ripening stage, severe heat can potentially compromise yield and grape quality. The physiological response of grapevine to heat stress suggests a potential use of irrigation to mitigate heatwaves, however there is limited information regarding the irrigation amounts and timings needed for this purpose. Following up on a pivotal trial conducted between 2019 and 2022, in this study irrigation treatments with varying intensity and timing of application were refined to determine their potential mitigation of heat-associated damage to yield and fruit composition.

WINE LEES AS A SOURCE OF NITROGEN FOR OENOCOCCUS OENI TO IMPROVE MALOLACTIC FERMENTATION PERFORMANCE

Malolactic fermentation (MLF) is a desired process in red and acidic white wines, after alcoholic fermentation (AF), carried out by the lactic acid bacterium (LAB) Oenococcus oeni. The advantages are an increase of pH, microbiological stabilization and organoleptic improvement of the final wine. However, the presence of stress factors such as ethanol, low pH, high total SO2, lack of nutrients and presence of inhibitors, could affect the successful completion of MLF [1]. Changes in amino acid composition and deficiencies in peptides after AF, showed that MLF can be delayed, signaling its importance for bacterial growth and L-malic acid degradation during MLF [2].

Pre-breeding for developing heat stress resilient grape varieties to ensure yield 

Climate change has numerous detrimental consequences and creates new challenges for viticulture around the world. Transitory or constant high temperatures frequently associated with an excess of sunlight (UV) can cause a variety of physiological disorders, such as sunburn. Diverse environmental factors and the plant’s response mechanisms to stress determine the symptoms. Grapevine berry sunburn leads to a drastic reduction in yield, and may eventually decline berry quality. Consequently, this poses a significant risk to the winegrowers.

Valutazione dell’equilibrio vegeto-produttivo con metodiche di proximal sensing

Nel biennio 2008-2009, nell’ambito di un progetto multidisciplinare coordinato e finanziato dal Consorzio Tuscania, 4 vigneti in differenti zone della Toscana sono stati monitorati con strumenti di proximal sensing al fine di valutare la variabilità riscontrabile e ottenere delle indicazioni sulle risposte vegetative delle piante e quanti-qualitative delle produzioni.